The start menu is one of the first things I used to fix on a brand-new Win10 install: start removing all those useless/annoying tiles until I have nothing left but a list of programs. (On Win11, the first thing I fix is to move the toolbar back to left-justified instead of centered; then I fix the start menu tiles).
But I do wish graphics designers would learn to leave well enough alone. People don't want their UI to change on them every 5-10 years. They want to learn one UI and stick with it. The Windows 7 UI was just about perfect; if they had kept that UI while changing internals not visible to the user, they would have had far faster adoption of Windows 10. As it is, I know many people who stuck to Windows 7 for as long as possible until the free-upgrade period was about to run out.
EDIT: I'm not saying there weren't things about the Win7 UI that couldn't be improved. The new Terminal app is immensely better than Conhost. IMMENSELY. But that's an incremental change, not a UI replacement.
The Windows 95 left tile was basically perfect. A lot of Linux distros have something similar. It allows you to quickly survey the useful programs. There is no further perfection.
A close second in my book was the PlayStation 3 User Interface. Gloriously intuitive. PlayStation 4 and the new XBox are god awful. I can't wait to buy a Steam Machine and never have to search for my freaking game again like on the XBox monstrosity that has all kinds of crapware on it. Is frustrating your users good for business?
Windows 8 and the Ubuntu of around that time both had absolutely bonkers interfaces. Is it better for a phone? Sure....but I'm not using a phone. Windows 8 was so bad I honestly can't believe it wasn't blocked by upper management. It made all the previous customer/user knowledge worthless. I literally had to memorize all these Window Key + letter commands just to shut down the computer and find the My Documents.
I hung onto win7 till the last possible moment. I don't really miss it but it was a lot more cohesive then 10. Thinking about it i'm increasingly convinced the guys in charge of the taskbar were not on speaking terms with anyone else at Windows and the control panel team all retired or left 6 months before the people designing the settings app arrived.
Just so that you don't accuse me of looking through rose tinted lenses, i think xp looks horrible. Admittedly design has moved on, but i don't remember ever loving it.
I remember it being called "Windows FP" where FP stood for Fischer-Price (maker of colorful plastic toys for babies and toddlers) at the time. Lots of people hated the design of XP after using Win98/2000. I got used to it, but much preferred 7 when it came out. There's a reason why Linux Mint's UI is modeled more or less after the style of Windows 7, not XP or 10.
But I do wish graphics designers would learn to leave well enough alone. People don't want their UI to change on them every 5-10 years. They want to learn one UI and stick with it. The Windows 7 UI was just about perfect; if they had kept that UI while changing internals not visible to the user, they would have had far faster adoption of Windows 10. As it is, I know many people who stuck to Windows 7 for as long as possible until the free-upgrade period was about to run out.
EDIT: I'm not saying there weren't things about the Win7 UI that couldn't be improved. The new Terminal app is immensely better than Conhost. IMMENSELY. But that's an incremental change, not a UI replacement.